At your first job, you filled your shelves with obscure books to impress your colleagues. As a first-time manager, you probably tried to be a super hero to save a project but were confused when your team seemed unhappy afterwards. In senior leadership, you probably realized you needed to hire a team but regretted not spending more time expanding upon your nine LinkedIn connections. As a VP, you were probably surprised when you had to repeat a goal not once, not twice, but fifty times before anyone took notice. For six years, I chronicled my hundreds of mistakes co-founding Meebo. I initially assumed that my faults were my own but after hiring folks to fill my shoes, I realized that everyone weathers similar rites of passage as we move from individual contributor, to manager, to senior leadership. I've spent countless hours hand-illustrating the scenes for this professional tell-all with the hope of helping others avoid "I wish someone had told me that!" moments.